Structure-Directing Interplay Between Tetrel and Halogen Bonding in Co-Crystal of Lead(II) Diethyldithiocarbamate with Tetraiodoethylene

Overview

Journal Int J Mol Sci

Publisher MDPI

Specialties Biochemistry
Chemistry
Molecular Biology

Date 2022 Oct 14

PMID 36233178

Authors

Lev E Zelenkov

Daniil M Ivanov

Ilya A Tyumentsev

Yulia A Izotova

Vadim Yu Kukushkin

Nadezhda A Bokach

Affiliations

Soon will be listed here.

Abstract

The co-crystallization of the lead(II) complex [Pb(SCNEt)] with tetraiodoethylene (CI) gave the co-crystal, [Pb(SCNEt)]∙½CI, whose X-ray structure exhibits only a small change of the crystal parameters than those in the parent [Pb(SCNEt)]. The supramolecular organization of the co-crystal is largely determined by an interplay between Pb⋯S tetrel bonding (TeB) and I⋯S halogen bonding (HaB) with comparable contributions from these non-covalent contacts; the TeBs observed in the parent complex, [Pb(SCNEt)], remain unchanged in the co-crystal. An analysis of the theoretical calculation data, performed for the crystal and cluster models of [Pb(SCNEt)]∙½CI, revealed the non-covalent nature of the Pb⋯S TeB (-5.41 and -7.78 kcal/mol) and I⋯S HaB (-7.26 and -11.37 kcal/mol) interactions and indicate that in the co-crystal these non-covalent forces are similar in energy.

References

Selvakumar K, Singh H . Adaptive responses of sterically confined intramolecular chalcogen bonds. Chem Sci. 2018; 9(35):7027-7042. PMC: 6137456. DOI: 10.1039/c8sc01943f. View

La Manna P, De Rosa M, Talotta C, Rescifina A, Floresta G, Soriente A . Synergic Interplay Between Halogen Bonding and Hydrogen Bonding in the Activation of a Neutral Substrate in a Nanoconfined Space. Angew Chem Int Ed Engl. 2019; 59(2):811-818. DOI: 10.1002/anie.201909865. View

Caruso F, Chan M, Rossi M . A Short Pb.Pb Separation in the Polymeric Compound Bis(pyrrolidinecarbodithioato)lead(II) and a Conformational Pathway Interconversion for the "Pb(II)S(4)" Framework. Inorg Chem. 1997; 36(17):3609-3615. DOI: 10.1021/ic970059f. View

Sheldrick G . SHELXT - integrated space-group and crystal-structure determination. Acta Crystallogr A Found Adv. 2014; 71(Pt 1):3-8. PMC: 4283466. DOI: 10.1107/S2053273314026370. View

Sheldrick G . Crystal structure refinement with SHELXL. Acta Crystallogr C Struct Chem. 2015; 71(Pt 1):3-8. PMC: 4294323. DOI: 10.1107/S2053229614024218. View

Mo O, Montero-Campillo M, Alkorta I, Elguero J, Yanez M . Ternary Complexes Stabilized by Chalcogen and Alkaline-Earth Bonds: Crucial Role of Cooperativity and Secondary Noncovalent Interactions. Chemistry. 2019; 25(50):11688-11695. DOI: 10.1002/chem.201901641. View

Bruno I, Cole J, Edgington P, Kessler M, Macrae C, McCabe P . New software for searching the Cambridge Structural Database and visualizing crystal structures. Acta Crystallogr B. 2002; 58(Pt 3 Pt 1):389-97. DOI: 10.1107/s0108768102003324. View

Guo X, Li Q . Dual functions of Lewis acid and base of Se in F2C=Se and their interplay in F 2CSe•••NH 3•••HX. J Mol Model. 2015; 21(6):157. DOI: 10.1007/s00894-015-2701-6. View

Aliyarova I, Tupikina E, Soldatova N, Ivanov D, Postnikov P, Yusubov M . Halogen Bonding Involving Gold Nucleophiles in Different Oxidation States. Inorg Chem. 2022; 61(39):15398-15407. DOI: 10.1021/acs.inorgchem.2c01858. View

10.

Tepper R, Schubert U . Halogen Bonding in Solution: Anion Recognition, Templated Self-Assembly, and Organocatalysis. Angew Chem Int Ed Engl. 2018; 57(21):6004-6016. DOI: 10.1002/anie.201707986. View

11.

Mackenzie C, Spackman P, Jayatilaka D, Spackman M . model energies and energy frameworks: extension to metal coordination compounds, organic salts, solvates and open-shell systems. IUCrJ. 2017; 4(Pt 5):575-587. PMC: 5600021. DOI: 10.1107/S205225251700848X. View

12.

Bamberger J, Ostler F, Garcia Mancheno O . Frontiers in Halogen and Chalcogen-Bond Donor Organocatalysis. ChemCatChem. 2020; 11(21):5198-5211. PMC: 6919929. DOI: 10.1002/cctc.201901215. View

13.

Bhattarai S, Sutradhar D, Chandra A . Strongly Bound π-Hole Tetrel Bonded Complexes between H SiO and Substituted Pyridines. Influence of Substituents. Chemphyschem. 2022; 23(10):e202200146. DOI: 10.1002/cphc.202200146. View

14.

Miller D, Chernyshov I, Torubaev Y, Rosokha S . From weak to strong interactions: structural and electron topology analysis of the continuum from the supramolecular chalcogen bonding to covalent bonds. Phys Chem Chem Phys. 2022; 24(14):8251-8259. DOI: 10.1039/d1cp05441d. View

15.

Bairagi K, Ingle K, Bhowal R, Mohurle S, Hasija A, Alwassil O . Interplay of Halogen and Hydrogen Bonding through Co-Crystallization in Pharmacologically Active Dihydropyrimidines: Insights from Crystal Structure and Energy Framework. Chempluschem. 2021; 86(8):1167-1176. DOI: 10.1002/cplu.202100259. View

16.

Zhao Q . Mutual influence of tetrel and halogen bonds between XCN (X=Cl, Br) and 4-TF-pyridine (T=C, Si, Ge). J Mol Model. 2020; 26(11):329. DOI: 10.1007/s00894-020-04596-x. View

17.

Humphrey W, Dalke A, Schulten K . VMD: visual molecular dynamics. J Mol Graph. 1996; 14(1):33-8, 27-8. DOI: 10.1016/0263-7855(96)00018-5. View

18.

Scheiner S . Competition between a Tetrel and Halogen Bond to a Common Lewis Acid. J Phys Chem A. 2020; 125(1):308-316. DOI: 10.1021/acs.jpca.0c10060. View

19.

Nagorny P, Sun Z . New approaches to organocatalysis based on C-H and C-X bonding for electrophilic substrate activation. Beilstein J Org Chem. 2017; 12:2834-2848. PMC: 5238598. DOI: 10.3762/bjoc.12.283. View

20.

Benz S, Poblador-Bahamonde A, Low-Ders N, Matile S . Catalysis with Pnictogen, Chalcogen, and Halogen Bonds. Angew Chem Int Ed Engl. 2018; 57(19):5408-5412. PMC: 5947745. DOI: 10.1002/anie.201801452. View